O-1812

O-1812 is an eicosanoid derivative related to anandamide that acts as a potent and highly selective agonist for the cannabinoid receptor CB₁, with a K_i of 3.4 nM at CB₁ and 3870 nM at CB₂.[1] Unlike most related compounds, O-1812 is metabolically stable against rapid breakdown by enzymes, and produces a cannabinoid-like discriminative effect in rats, which is similar but not identical to that produced by cannabinoid drugs of other chemical classes.[2][3][4][5]

O-1812

Identifiers
IUPAC name (5Z,8Z,11Z,14Z)-20-cyano-N-[(2R)-1-hydroxypropan-2-yl]-16,16-dimethylicosa-5,8,11,14-tetraenamide
CAS Number	342882-77-3
PubChem CID	9823107
IUPHAR/BPS	732
ChemSpider	7998855
CompTox Dashboard (EPA)	DTXSID80745442
Chemical and physical data
Formula	C26H42N2O2
Molar mass	414.634 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C[C@H](CO)NC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C(C)(C)CCCCC#N
InChI InChI=1S/C26H42N2O2/c1-24(23-29)28-25(30)19-15-12-10-8-6-4-5-7-9-11-13-16-20-26(2,3)21-17-14-18-22-27/h4-5,8-11,16,20,24,29H,6-7,12-15,17-19,21,23H2,1-3H3,(H,28,30)/b5-4-,10-8-,11-9-,20-16-/t24-/m1/s1 Key:WZQHSBKOWZOASP-QLZKPENWSA-N
(what is this?)  (verify)

See also

• AM-1235
• AM-2232
• AM-2389
• Methanandamide
• O-774
• O-1057

References

1. Di Marzo V, et al. (February 2001). "Highly selective CB₁ cannabinoid receptor ligands and novel CB₁/VR₁ vanilloid receptor "hybrid" ligands". Biochemical and Biophysical Research Communications. 281 (2): 444–51. doi:10.1006/bbrc.2001.4354. PMID 11181068.
2. Baskfield CY, Martin BR, Wiley JL (April 2004). "Differential effects of Δ⁹-tetrahydrocannabinol and methanandamide in CB₁ knockout and wild-type mice". The Journal of Pharmacology and Experimental Therapeutics. 309 (1): 86–91. doi:10.1124/jpet.103.055376. PMID 14718593. S2CID 36621393.
3. Wiley JL, et al. (August 2004). "A comparison of the discriminative stimulus effects of Δ⁹-tetrahydrocannabinol and O-1812, a potent and metabolically stable anandamide analog, in rats". Experimental and Clinical Psychopharmacology. 12 (3): 173–9. doi:10.1037/1064-1297.12.3.173. PMID 15301634.
4. Wiley JL, Smith FL, Razdan RK, Dewey WL (March 2005). "Task specificity of cross-tolerance between Δ⁹-tetrahydrocannabinol and anandamide analogs in mice". European Journal of Pharmacology. 510 (1–2): 59–68. doi:10.1016/j.ejphar.2005.01.006. PMID 15740725.
5. Breivogel CS, et al. (July 2008). "Sensitivity to Δ⁹-tetrahydrocannabinol is selectively enhanced in β-arrestin2 -/- mice". Behavioural Pharmacology. 19 (4): 298–307. doi:10.1097/FBP.0b013e328308f1e6. PMC 2751575. PMID 18622177.